$5,000 Reward Offer for Jameses

The following is the proclamation of the Governor of Missouri, announcing rewards for the arrest of train robbers following the crimes which occurred near Winston, MO, in 1881 (the reward was really offered by the railroad companies through the governor, together with what was already authorized by the legislature to pay the rewards offered):

WHEREAS, It has been made known to me, as Governor of the State of Missouri, that certain parties, whose names are to me unknown have confederated and banded themselves together for the purpose of committing robberies and other depredations within this State; and

WHEREAS, Said parties did, on or about the Eighth day of October, 1879, stop a train near Glendale, in the county of Jackson, in said state, and, with force and violence, take, steal and carry away the money and other express matter being carried thereon; and

WHEREAS, On the fifteenth day of July, 1881, said parties and their confederates did stop a train upon the line of the Chicago, Rock Island and Pacific Railroad, near Winston, in the County of Daviess, In said State, and, with force and violence, take, steal, and carry away the money and other express matter being carried thereon; and, in perpetration of the robbery last aforesaid, the parties engaged therein did kill and murder one William Westfall, the conductor of the train, together with one John McMillan, who was at the time in the employ of said company, then on said train; and

WHEREAS, Frank James and Jesse W. James stand indicted in the Circuit Court of said Daviess County, for the murder of John W. Sheets, and the parties engaged in the robberies and murders aforesaid have fled from justice and have absconded and secreted themselves;

NOW, THEREFORE, in consideration of these premises, and in lieu of all other rewards heretofore offered for the arrest or conviction of the parties aforesaid, or either of them, by any person or corporation, I, Thomas T. Crittenden, Governor the State of Missouri, do hereby offer a reward of five thousand dollars ($5,000) for the arrest and conviction of each person participating in either of the robberies or murders aforesaid, excepting the said Frank James and Jesse W. James; and for the arrest and delivery of said


and each or either of them, to the sheriff of said Daviess County, I hereby offer a reward of five thousand dollars, ($5,000.00), and for the conviction of either of the parties last aforesaid of participation in either of the murders or robberies above mentioned, I hereby offer a further reward of five thousand dollars ($5,000.00).

IN TESTIMONY WHEREOF, I have hereunto set my hand and caused to be affixed the Great Seal of the State of Missouri. Done at the City of Jefferson on this 28th day of July, A.D., 1881.


By the Governor:
Mich’l K. McGrtath, Sec’y of State

History Book Account of 1881 Robbery

This following account of the 1881 train robbery which occurred in July, 1881, on the Chicago, Rock Island & Pacific Railroad near Winston, MO, as recorded in the 1882 History of Daviess County (pp. 504-507):


Winston, a village of some three hundred and fifty in habitants, on the Chicago, Rock Island & Pacific Railroad, in Colfax Township, this county, was the scene of a daring train robbery and murder on the night of July 15th, 1881, which occasioned intense excitement all of the State and led to fierce denunciations of the file perpetrators of the deed. Winston is some eleven miles from Gallatin, and a large crowd collected at the depot to await the arrival of the train and discuss the details of the crime. The fact that several of Gallatin’s citizens were on board, excited a deeper interest in the tragic occurrence. The robbers were seven in number and were equipped after the most approved style for the desperate work they had undertaken. Dark masks hid their features, and heavy revolvers hung at either side of their waists within easy reach. They boarded the train in couples and as the train drew out of Winston, began their work. There were about thirty passengers in the smoking car, while the rear passenger coach was very near filled. The conductor, William Westfall, passed into the smoking car from the baggage car and began to take up the tickets. He came slowly down the aisle and when about halfway, a tall man in the rear of the coach suddenly arose and ordered “everybody down!” The sharp command was emphasized by a ringing shot from a large revolver. On the instant all was excitement. Conductor Westfall did not obey the command, but seemed on the point of pulling the bell rope. His hand was scarcely lifted, when the robber swung quickly around with a revolver in each hand and with the quickness of the lightning’s flash two bullets went on their fatal way to Westfall’s breast. The wounded man staggered to the door and fell from the train, dead. The first man was joined by a second and the two kept up a steady firing at random, shattering window glass and transoms, as they moved through the car. As soon as they left the coach several passengers went out to the rear of the platform. Firing was going on all the time. Shots could be heard in the front and the rear. The two men returned and again passed through the “smoker,” all the time shooting recklessly, but seemingly with no intention of hitting any of the passengers, and stationed themselves on the front platform of the same car. As the shooting ceased for a moment several passengers on the rear platform peered through the windows into the car and immediately a bullet shattered the glass. Shortly after another man on the platform raised up and looked into the car, a pistol shot rang out upon the air and a bullet crashed through the brain of Frank McMillan, and he fell from the train, a corpse.

In the meantime, while these tragic events were transpiring in the smoking car, others equally excitable were taking place on the engine and in the baggage car. Two men began a rapid fusilade upon the engineer and fireman, but fortunately no damage was done further than breaking the glass. When the shooting began the occupants of the cab put out the lights and made their way to a safe position under the headlight, on the “cow-catcher,” where they remained safely ensconced, while two masked men took possession of the engine, one officiating as engineer while the other kept guard. Three of the brigands captured the baggage car and at the muzzles of their revolvers forced the express messenger to open the safe, from which they took the contents, variously estimated at from $3,000 to $15,000, and rapidly placed the packages into a sack carried for that purpose. After securing the contents of the safe the bold freebooters made no further attempts at robbery, but at a given signal, left the train at a point probably a miles distant from Winston, where they found horses in waiting for them at a small grove and, which a parting volley, they galloped away.


The news spread rapidly, and parties were organized and put off in active pursuit, but the desperadoes being well mounted rapidly distanced all pursuers, and up to the first of December, 1881, no trace has been found of them. Rewards amounting to $50,000 have been offered for their capture but they are still at large. It was the almost unanimous verdict of those familiar with the details of the murder and robbery, that the James boys were the leaders of the gang. The following from Judge McDougal of Gallatin shows the general opinion in that regard to the capture: “The robbers will never be caught. They know the country too well for that. They had been around the country about Winston for four or five days, and were thoroughly acquainted with the lay of the ground. And then they had the best horses in the country; if the citizens had been right on the spot and started after them, the robbers could easily have ridden away from them. No doubt by the time pursuit commenced they were well out of the county. I think the James brothers were connected with it, and one, at least, of them was there.”


Below is given the sworn testimony of the principal witness of the fatal tragedy:

J.L. Penn, being duly sworn, said: “I live in Wilton Junction, Iowa. I was on the eastern bound train on the evening of July 15, 1881. I was in the front car. Just after leaving the depot at Winston, three men entered from the front door. Each was dressed in a dark suit of clothes, with high caps, and were masked. The conductor was in the act of putting a check in my brother’s hat. Two of the men fired at the conductor. The conductor went toward the rear of the car, was in a stooping position as though shot. The men followed him, shooting at random in the car. The conductor and the three men passed out of the car at the rear end. Did not see the conductor after he left the car. The three men went into the next car, firing as they went, In a few minutes they turned and went into the first mentioned car. They fired two or three more shots as they went back through the car. One stood on the platform and two went into the baggage car. When they first entered the car one of them said stop to the conductor. I heard several shots fired after they went into the baggage car. As they entered the baggage car Frank McMillan and myself went to the rear platform of the car and sat on the steps. Firing ceased. I raised up and looked forward into the baggage car, when one of them fired at me, breaking a glass near me. I then sat down again. In a short time McMillan raised up and looked in at the window. A shot was fired, and Frank McMillan fell forward on the platform. The train came to a stop at the Dog Creek bridge. While standing I heard some one say move on farther and the train moved on to Little Dog Creek bridge and stopped. In a few minutes three men passed me as I sat on the steps. They were on the south side of the track and went down the dump. I then got off in company with R.W. Penn and A. McMillan, and started to look for Frank. We came back toward Winston, about a fourth of a mile. We met George Steward and others with a hand-car. A portion of us walked on each side of the track, looking for Frank McMillan or others. We found his body a short distance this side of the bridge. Some of the men put him on the hand-car and brought him to town.”

The testimony of several other witnesses was substantially the same as the foregoing. Conductor Westfall’s remains were taken to Plattsburg and interred.

1881 Train Robbery at Winston, MO

This accounty is reprinted from the July 21, 1881, edition of the Gallatin North Missourian. It’s subheadings were: “Conductor Westfall and Frank McMillen Killed” and “The Express Car Robbed.”

This account is reprinted from the July 21, 1881, edition of the Gallatin North Missourian (with later photos added for display here). The report’s subheadings were: “Conductor Westfall and Frank McMillen Killed” and “The Express Car Robbed”:

Friday night the regular Kansas City and Chicago passenger train, on the Rock Island road, was robbed just this side of Winston, and the Conductor, Wm. Westfall and a passenger, Frank McMillan of Wilton, Iowa, were killed by the train robbers. The train was on time, and as it left Winston at 9:30 p.m., three armed men stepped onto the front end of the smoking car. They fired through the glass in the car door, three men disguised with heavy black whiskers entered the car and fired through the windows in the front end of the car. While thus terrifying the passengers they ordered “hands up.” Conductor Westfall was about the middle of the car, taking up tickets when he was shot in the back. He was between S.T. Brosius, Esq., and Joseph H. McGee of this place. They say he dropped his lantern and staggered to the door. Whether he fell off the platform of the car or was pushed off by one of the robbers they do not know. His body was found just this side of the section house at Winston.

One of the scenes painted by Thomas Hart Benton (1889-1975) featured in the Missouri State Capitol at Jefferson City features outlaw Jesse James in a mythical train/bank robbery. Benton’s work adorns the House Lounge on the third floor of the Capitol. The murals were commissioned by the legislature in early 1935 for $16,000 and completed in December 1936.

J.L. Penn and Frank McMillen were on the platform of the baggage car, and while looking in at the door window he was shot in the forehead and rolled off the car.

Two of the robbers went into the express car and ordered Murray, the express messenger, to open the safe. He began parleying with them, when instantly they knocked him down with a pistol and made him open the safe. It is not known but it is thought they got about $4,000.

They shot out the glass of the cab of the engine and made the engineer stop the train at the Dog Creek bridge. Quite a number of hands are at work at this bridge, and hearing the firing on the train they were aroused, and it is probable for this reason that the robber made the engineer run the train one half mile further to Little Dog Creek where they left the train. Their horses were tied in the brush about 200 yards south of the Dog Creek bridge. They did not take time to untie their horses but cut the halter straps, but before they mounted they threw out the empty shells from their pistols. Our City Marshal, Albert Gibbons, got the pieces of the halter straps left on the trees. He carefully examined where the horses stood and he thinks there were only three horses at that place.

This impressive stone culvert is located a mile east of Winston, MO, on the now abandoned railroad bed of the Chicago, Rock Island & Pacific Railroad. This is about the location where the train robbery involving murder by outlaws Frank & Jesse James occurred. However, this stone culvert easily visible next to Highway 6 was constructed after the infamous crime occurred.

[Sidenote: The July 22, 1881, edition of the Liberty Tribune reported that the robbery and murder occurred “near some stone work being constructed by the railroad… after the flight of the gang, another man was found lying dead near the stone work. The opinion is, that he was a stone cutter who had tried to prevent the escape of the robbers and had been shot down in his tracks…”]

On Friday, two men having very fine horses, got their dinner at Kld. Benj. Machette. They told him that they lived at Plattsburg and were hunting horse thieves. That afternoon Kara Souls was in the brush near the Little Dog Creek bridge., and the same two men who were laying in the woods by their horses. They told him that they lived at Plattsburg, were resting and were going to Ben Matchetts to buy a cow. They had got their dinner at Matchett’s and that is the way they knew his name.

Sheriff Crozier and our City Marshal Gibbons tracked the three horses about seven miles towards the H & St. Joseph, and the lost the track. Young Caster living south of Winston, says he was up in the night and saw three men loping their horses past his house, and they were tracked past his house from Dog Creek. This is the last that was seen of them so far as we can hear.

About 11 o’clock the word came here of the robbery. Sheriff Crozier waked up about 30 of our citizens and hurried to the depot to get the train going to Winston. It was about 12 o’clock before the train left and then had orders to lay on the Highland switch until the robbed train passed. It was 2 o’clock before they got to Winston. The robbers then had 4 hours the start of them. Sheriff Crozier and Oscar Naylor hurriedly mounted horses and rode to Kidder, and gave the alarm. As soon as it was daylight they watched the road carefully to Winston for tracks of the robbers but did not see any until they came near Mr. Casters.

Mr. Walker, Division Superintendent of the Rock Island RR, was not at home or there would have been an extra through sooner.

Everything looks as if it was the work of the James boys or their gang. Westfall was the conductor on the train which carried the Pinkerton detectives to Mrs. Samuels the time her boy was killed and she lost her arm by the explosion of the shell which the detectives threw into her house. They James boys swore they would kill him, and they or their gang have done it.

Tuesday, Mrs. Samuels, the mother of the James boys, was in Kansas City. She talked freely with the reporters about the robbery. She says Frank and Jesse James are both dead, and could have had nothing to do with the robbery unless their ghosts were there.

Sheriff Crozier was out three days and nights but could get no clue to the whereabouts of the robbers.

The express company has offered $5,000 and the railroad company $5,000 for the robbers.

—  account published July 21, 1881, in the Gallatin North Missourian

Wm. Westfall [1843-1881] was killed during the train robbery at Winston by Frank & Jesse James on July 15, 1881. Westfall was the train conductor. He is buried in the old Plattsburg Cemetery. (1989 photo)

Winston and its Rock Island Train Depot

In 1871 a new railroad station was built by the Rock Island Railroad on a high point in Daviess County, halfway between Gallatin and Cameron. At this point a community began to take shape around the depot. At first the town was named Crofton, in honor of one of the donors of the land for the town. But in 1872 with the arrival of a post office, the town changed its name to Winston.

In 1871 a new railroad station was built by the Southwestern Branch of the Chicago Rock Island & Pacific Railroad on a high point in Daviess County, halfway between Gallatin and Cameron. At this point a community began to take shape around the depot. At first the town was named Crofton, in honor of one of the donors of the land for the town. But in 1872 with the arrival of a post office, the town changed its name to Winston.

This blank check was circulated prior to the time the community of Emporia, MO, later became Winston, MO. [courtesy Dorothy Olson]
Winston was incorporated in 1878. The town grew rapidly, having three and sometimes four doctors, three attorneys, drug stores, general merchandise stores, grain and lumber dealers, livery stables, a newspaper, a millinery shop and a hotel. The population at one time grew to exceed 600, but by 1937 the population dwindled to 400 and by 1978 those living at Winston numbered less than 200.

Mr. and Mrs. Ebberdeen [courtesy Greg Lawson of Edwardsburg, Mich. The couple were friends of his great-great-grandmother who is buried in the Winston Cemetery in 1922, Ephrium Kuhns]
The Winston depot lives on in James Gang legend and lore as the site where the 1881 train robbery commenced. Ten years earlier, when the depot was new, the first station agent was T.F. Jefferies, a native of Somersetshire, England. Two sets of tracks were to the front of the depot and were used for switching cars. Another set of siding tracks ran on the north side of the depot building.

The depot stands at the south edge of Winston, at the junction of Highway 69 and Route Y. The legal location is as follows: NW 1/4, Sec. 3 Twp 58, Rng 29.

The building sat vacant when a historic inventory was conducted at various sites located throughout Northwest Missouri. Its interior and exterior condition was listed as “poor.” The building was used to shed road maintenance equipment.

Eventually, the Winston Historical Society organized and converted the depot into a community museum. The organization organizes and hosts an annual festival, Jesse James Days, at the adjascent city park and at the depot.

— sources: Omar Baxter and Harl A. Garner of Winston; Daviess County Centennial edition; and a historic inventory report prepared by Mary Virginia Croy for the Daviess County Historical Society (1978)

This is the Rock Island train depot in Winston, MO, where James Gang members embarked in order to pull off their 1881 robbery. The depot was built in 1871 on a high point in Daviess County, halfway between Gallatin and Cameron. The first station agent was T.F. Jefferies, a native of Somersetshire, England. Two sets of tracks fronted the depot and were used for switching cars while a set of siding tracks ran behind the depot. (date unknown)
This is the interior of the Winston Rock Island train depot when restoration by the Winston Historical Society commenced in 1989. The township previously used the depot as an equipment storage shed.
This railroad stone culvert located east of Winston, MO, is commonly associated with the James Gang robbery of a Rock Island train in 1881. Before this, a wooden trestle was used instead of this huge stone arch.
A rare view of the “dump” taken from inside the railroad stone culvert east of Winston, MO, circa 1930. [Barb Caldwell, Winston Historical Society]


The following was presented by Lynn Martindale, president of the Winston Historical Society, to the Gallatin Rotary Club in May, 1990. His speech was entitled, “Expansion, Contraction, and the Winston Depot”:

The first workable railway locomotive was invented in England in 1829. By 1831, the United States had its first organized railroad — the Baltimore & Ohio.

When the American Civil War broke out in 1860, the nation had a reasonably fine network of railroad tracks east of the Mississippi River. One of President Lincoln’s problems during the Civil War was that of keeping California from seceding or from joining the Confederacy. For that he needed a railroad. The Union Pacific and Central Pacific railroads were chartered in 1862 but were not joined until 1869, just two years before the Winston depot was built in 1871,

Following the American Civil War, there was a major thrust to push railroad trackage west of the Mississippi In this period the Chicago & Southwestern Railroad laid tracks between Gallatin and Cameron, among other places. Historically, local traffic was important to sustain the profits of railroads so that railroad companies were anxious to develop towns alongside their tracks. The Chicago & Southwestern wanted to develop a town site approximately halfway between Gallatin and Cameron. Several persons donated a tract of land to the railroad and this tract became known as Crofton Junction. Among its advantages was that it had the highest elevation of any tract of land in Daviess County.

The name of the town was soon changed to Winsonville, named after Frederick Winson, president of the Chicago & Southwestern. But by 1885 it was being called Winston and was incorporated under that name.

The Chicago & Southwestern Railroad Company was organized for the purpose of building a railroad, not of operating it, so when the construction job was completed the responsibilities of ownership and operation passed to the Chicago & Rock Island Railroad Company.

The expanding railroads of the 1870s faced a major problem. They all wanted to carry traffic to California but between Missouri and California there was a vast area which was then called the Great American Desert. Tracks had to be laid, rolling stock had to be run over those tracks and people had to be hired to operate the railroads in areas in which the traffic would not generate enough revenue to pay the total cost of railroad operation. Additionally, most railroads were built with borrowed money. Clearly, railroads were vulnerable to periods of economic downturn. Many railroads failed in the panics of the 1870s, the 1880s, and 1890s.

Railroad property was also subject to natural disaster, storms, Indian uprisings and fires. The Winston depot burned during the 1890s and had to be replaced.

During the first World War (1914-18), railroad traffic reached its all time maximum. After 1918 the flow of railroad traffic fluctuated from year to year but generally downward as newer forms of transportation took hold. Faced with falling revenue, railroads began to economize. They discontinued service to less profitable locations. The Rock Island halted service to Winston in 1938. Eventually the railroads sought to get out of the passenger-carrying business entirely because of all the things that can be carried by train, people are the most expensive to transport. In order to generate some one-time sources of revenue, many railroads took up their tracks and sold their rights-of-way. Many small railroad stations were taken over by local units of government for non-payment of taxes.

For many years the Winston depot was used as public property. At various times, the City of Winston or Colfax Township used the building for equipment storage or for other public purposes.

In 1987 some people organized the Winston Historical Society because they had a vision of what might be done with the Winston depot, which was looking rather dilapidated by that time. The vision was to restore the building to something akin to its earlier condition and to use it as a museum to attract visitors to Winston. The new historical society acquired title to the building, and its members devoted a tremendous amount of effort and expertise to the project… The Winston Historical Society has three sources of revenue: membership dues ($10 per person), donations, and fundraising activities. At this time there are approximately 75 members… Until recently, donations have not been significant but now the organization is legally recognized as a non-profit entity, thus making donations tax deductible for donors. The bulk of revenue comes from fund raising projects — chili suppers, ice cream social, Jesse James Days events, softball and basketball tournaments, and from sales of caps, jackets and T-shirts…

At the present time the outside of the building is in good shape, and there is electricity in the building. The east half of the interior is sub-floored and the beadboard on the walls is almost wholly installed. The walls are insulated. We’re expecting to use that area for a display of some exhibits at the annual Jesse James Days celebration on July 14-15. Unfortunately, the west half of the interior is still largely untouched, even to the dirt floor. It will require a lot of work and a lot of money to bring the condition of that half of the building up to the point where it can be used…

When the Winston depot was built in 1871, a wave of optimism was sweeping the country. A lot of people risked a lot of money in the railroad industry because they believed that railroad transportation was the wave of the future. They believed that this country would be knit together by a network of steel rails that would make the world available to every hamlet in the country. We, too, are optimistic. We believe that tourism in Northwest Missouri is a growth industry. We believe that our depot will help attract tourist dollars to this part of the state, and that we, in turn, will benefit from things that are going on in Gallatin and Jamesport.